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Diphenylbutadiyne
Diphenylbutadiyne is the hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ... with the formula (C6H5C2)2. It is a member of the diyne chemical class and can be made via the Glaser coupling of phenylacetylene However, a variety of other synthesis methods have been developed. Diphenylbutadiyne forms a variety of metal-alkyne complexes. One example is the organonickel complex (C5H5Ni)4C4(C6H5)2.{{cite journal , doi=10.1107/S0365110X65001226, title=Crystal Data for Some Dicyclopentadienyldinickel Alkyne Compounds, year=1965, last1=Mills, first1=O. S., last2=Shaw, first2=B. W., journal=Acta Crystallographica, volume=18, issue=3, page=562 References Conjugated diynes Phenyl compounds Alkyne derivatives ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Glaser Coupling
The Glaser coupling is a type of coupling reaction. It is by far one of the oldest coupling reactions and is based on copper compounds like copper(I) chloride or copper(I) bromide and an additional oxidant like air. The base used in the original research paper is ammonia and the solvent is water or an alcohol. The reaction was first reported by in 1869. He suggested the following process on his way to diphenylbutadiyne: :CuCl + PhC2H + NH3 → PhC2Cu + NH4Cl :4PhC2Cu + O2 → 2PhC2C2Ph + 2Cu2O Modifications Eglinton reaction In the related Eglinton reaction two terminal alkynes are coupled by a copper(II) salt such as cupric acetate. :2R-\!\!-H -> overset\ce\ce] R-\!\!-\!\!-R The oxidative coupling of alkynes has been used to synthesize a number of natural products. The stoichiometry is represented by this highly simplified scheme: : Such reactions proceed via copper(I)-alkyne complexes. This methodology was used in the synthesis of cyclooctadecanonaene. Another example ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenylacetylene
Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an analog for acetylene; being a liquid, it is easier to handle than acetylene gas. Preparation In the laboratory, phenylacetylene can be prepared by elimination of hydrogen bromide from styrene dibromide using sodium amide in ammonia: : It can also be prepared by the elimination of hydrogen bromide from bromostyrene using molten potassium hydroxide. Yet another method involves the Sonogashira coupling of iodobenzene with trimethylsilylacetylene, followed by removal of the trimethylsilyl group using TBAF. Reactions Phenylacetylene is a prototypical terminal acetylene, undergoing many reactions expected of that functional group. It undergoes semihydrogenation over Lindlar catalyst to give styrene. In the presence of base and copper(II) salts, it undergoes oxidative coupling to give diphenylbutadiyne. In the presence of metal cata ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually faint, and may be similar to that of gasoline or Naphtha, lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases (such as methane and propane), liquids (such as hexane and benzene), low melting solids (such as paraffin wax and naphthalene) or polymers (such as polyethylene and polystyrene). In the fossil fuel industries, ''hydrocarbon'' refers to naturally occurring petroleum, natural gas and coal, or their hydrocarbon derivatives and purified forms. Combustion of hydrocarbons is the main source of the world's energy. Petroleum is the dominant raw-material source for organic commodity chemicals such as solvents and polymers. Most anthropogenic (human-generated) emissions of greenhouse gases are eithe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Metal-alkyne Complex
In organometallic chemistry, a transition metal alkyne complex is a coordination compound containing one or more alkyne ligands. Such compounds are intermediates in many catalytic reactions that convert alkynes to other organic products, e.g. hydrogenation and trimerization. Synthesis Transition metal alkyne complexes are often formed by the displacement of labile ligands by the alkyne. For example, a variety of cobalt-alkyne complexes arise by the reaction of alkynes with dicobalt octacarbonyl. : Many alkyne complexes are produced by reduction of metal halides: : Cp2TiCl2 + Mg + Me3SiC≡CSiMe3 → Cp2Ti CSiMe3)2+ MgCl2 Reactions Transition metal alkyne complexes participate in many reactions. Protonation of alkyne ligands gives alkenyl complexes: : Complexes of terminal alkenes are prone to rearrange to vinylidene derivatives: : The Pauson–Khand reaction provides a route to cyclopentenones via the intermediacy of cobalt-alkyne complexes. Structure and bonding The c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organonickel Complex
Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds featuring nickel-carbon bonds. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds are also short-lived intermediates in organic reactions. The first organonickel compound was nickel tetracarbonyl Ni(CO)4, reported in 1890 and quickly applied in the Mond process for nickel purification. Organonickel complexes are prominent in numerous industrial processes including carbonylations, hydrocyanation, and the Shell higher olefin process. Classes of compounds : Alkyl and aryl complexes A popular reagent is Ni(CH3)2(tetramethylethylenediamine). Many alkyl and aryl complexes are known with the formula NiR(X)L2. Examples include dppf)Ni(cinnamyl)Cl) ''trans''-(PCy2Ph)2Ni(''o''-tolyl)Cl, (dppf)Ni(''o''-tolyl)Cl, (TMEDA)Ni(''o''-tolyl)Cl, and (TMEDA)NiMe2, (TMEDA)Ni(Br)(C6F5 Nickel compounds of the type NiR2 also e ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Conjugated Diynes
Conjugation or conjugate may refer to: Linguistics *Grammatical conjugation, the modification of a verb from its basic form *Emotive conjugation or Russell's conjugation, the use of loaded language Mathematics *Complex conjugation, the change of sign of the imaginary part of a complex number *Conjugate (square roots), the change of sign of a square root in an expression *Conjugate element (field theory), a generalization of the preceding conjugations to roots of a polynomial of any degree *Conjugate transpose, the complex conjugate of the transpose of a matrix * Harmonic conjugate in complex analysis * Conjugate (graph theory), an alternative term for a line graph, i.e. a graph representing the edge adjacencies of another graph *In group theory, various notions are called conjugation: **Inner automorphism, a type of conjugation homomorphism **Conjugacy class in group theory, related to matrix similarity in linear algebra **Conjugation (group theory), the image of an element und ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenyl Compounds
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen atom, which may be replaced by some other element or compound to serve as a functional group. A phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, the phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Nomenclature Usually, a "phenyl group" is synonymous with and is represented by the symbol Ph (archaically, Φ), or Ø. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. Fo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
